5-Fluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid → 5-Fluoro-2-(2-isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047790Notes

Reaction equation

HRID 1047790 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:14][C:15](=[O:27])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[CH:23]=[C:24]([CH3:26])[CH3:25])([C:11]([OH:13])=[O:12])[CH2:5]2>C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:14][C:15](=[O:27])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[CH2:23][CH:24]([CH3:25])[CH3:26])([C:11]([OH:13])=[O:12])[CH2:5]2

Participants

4

Reactant 1

HCID 251607995-Fluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

Product 1

HCID 251606695-Fluoro-2-(2-isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid (149) (230 mg, 0.63 mmol) in acetic acid (10 mL) is added the catalyst, Pd—C (5 wt. % Pd, 134 mg, 6.3% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 55 psi, 95° C., overnight. The catalyst is removed by filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined organic solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (150) as white solid (200 mg, 86%).

Workup

  1. customThe resulting reaction mixture
  2. custom55 psi, 95° C., overnight
  3. customThe catalyst is removed by filtration through a pre-column (10 g silica gel)
  4. washwashed with EtOH
  5. concentrationThe combined organic solution is concentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-020850a09fb74da2b65241d77c18bc5b
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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